Catalytic olefination of carbonyl compounds. A new versatile method for the synthesis of alkenes

Russian Chemical Bulletin

Volumn 53, Issue 5, 2004, Pages 1034-1064

  Nenajdenko, V G ^a   Korotchenko, V N ^a   Shastin, A V ^b   Balenkova, E S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

alkenes; carbonyl compounds; catalysis; copper salts; electrophilicity; hydrazones; metal carbene complexes; olefination; polyhaloalkanes; transition metals

Indexed keywords

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; HALIDE; HALOGEN;

CATALYSIS; CATALYST; CHEMICAL PHENOMENA; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; MOLECULAR MODEL; OLEFINATION; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4544315358     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUCB.0000041302.14763.72     Document Type: Review

References (146)

1. Comprehensive Organic Synthesis, Eds B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1999, 1.
2. M. Beller and C. Bolm, Transition Metals for Organic Synthesis, Wiley, New York, 1998, 1, 2.
3. Preparation of Alkenes, Ed. J. M. J. Williams, Oxford University Press, Oxford, 1996, 254 pp.
4. B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
5. A. W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York, 1993, p. 221.
6. J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87.
7. L. Horner, N. M. R. Hoffman, H. G. Wippel, and G. Klahre, Chem. Ber., 1959, 92, 2499.
8. M. Julia and J. M. Paris, Tetrahedron Lett., 1973, 14, 4833.
9. C. R. Johnson, J. R. Shanklin, and R. A. Kirchhoff, J. Am. Chem. Soc., 1973, 95, 6462.
10. C. R. Johnson and R. A. Kirchlioff, J. Am. Chem. Soc., 1979, 101, 3602.
11. T.-H. Chan, Acc. Chem. Res., 1977, 10, 442.
12. W. P. Weber, Silicon Reagents for Organic Synthesis, Springer, Berlin, 1983, p. 58.
13. D. J. Ager, Synthesis, 1984, 384.
14. D. J. Ager, Org. React., 1990, 38, 1.
15. L. F. van Staden, D. Gravestock, and D. J. Ager, Chem. Soc. Rev., 2002, 31, 195.
16. D. J. Peterson, J. Org. Chem., 1968, 33, 780.
17. H. Hashimoto, M. Hida, and S. Miyano, J. Organomet. Chem., 1967, 10, 518.
18. K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1978, 19, 2417.
19. A. Fürstner, J. Organomet. Chem., 1987, 336, C33.
20. K. Takai, K. Nitta, and K. Utimoto, J. Am. Chem. Soc., 1986, 108, 7408.
21. D. M. Hodgson, L. T. Boulton, and G. N. Maw, Tetrahedron, 1995, 51, 3713.
22. K. Takai, Y. Kataoka, Y. Okazoe, and K. Utimoto, Tetrahedron Lett., 1987, 28, 1443.
23. F. N. Tebbe, G. W. Parshall, and G. S. Reddy, J. Am. Chem. Soc., 1978, 100, 3611.
24. H. Siebeneicher and S. Doye, J. Prakt. Chem., 2000, 342, 102.
25. T. Takeda, R. Sasaki, and T. Fujiwara, J. Org. Chem., 1998, 63, 7286.
26. T. Takeda, Y. Endo, A. Chandra Sheker Reddy, R. Sasaki, and T. Fujiwara, Tetrahedron, 1999, 55, 2475.
27. J. E. McMurry, Chem. Rev., 1989, 89, 1513.
28. J. E. McMurry, Acc. Chem. Res., 1974, 7, 281.
29. D. Lenoir, Synthesis, 1989, 883.
30. J. E. McMurry, Acc. Chem. Res., 1983, 16, 405.
31. A. Fürstner and B. Bogdanovic, Angew. Chem., Int. Ed. Engl., 1996, 35, 2442.
32. M. Ephritikhine, J. Chem. Soc., Chem. Commun., 1998, 2549.
33. A. V. Shastin, V. N. Korotchenko, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 1999, 2210 [Russ. Chem. Bull., 1999, 48, 2184 (Engl. Transl.)].
34. A. V. Shastin, V. N. Korotchenko, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 1999, 2210 [Russ. Chem. Bull., 1999, 48, 2184 (Engl. Transl.)].
35. V. N. Korotchenko, Ph.D. Thesis, Moscow State University, Moscow, 2003, 198 pp. (in Russian).
36. W. Latimer, The Oxidation States of the Elements and their Potentials in Aqueous Solutions, University of California, New York, 1952.
37. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2000, 56, 6557.
38. C. Reichardt, Solvents and Solvents Effects in Organic Chemistry, VCH, Weinheim, 1988.
39. V. N. Korotchenko, A. V. Shastin, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2003, 469 [Russ. Chem. Bull., Int. Ed., 2003, 52, 492].
40. V. N. Korotchenko, A. V. Shastin, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2003, 469 [Russ. Chem. Bull., Int. Ed., 2003, 52, 492].
41. Yu. P. Kitaev and B. I. Buzykin, Gidrazony [Hydrazones], Nauka, Moscow, 1974, 416 pp. (in Russian).
42. H. Reimlinger, Chem. Ber., 1964, 97, 339.
43. I. A. D'yakonov, Alifaticheskie diazosoedineniya [Aliphatic Diazo Compounds], Leningradskii Univ., Leningrad, 1958, 140 pp.
44. M. Regitz and G. Maas, Diazo Compounds, Academic Press, London, 1986, 596 pp.
45. B. Eistert, M. Regitz, G. Heck, and H. Schwall, Metoden um Herstellung und Umwandlung von aliphatic Diazowerbindungen, in Houben-Weil, Methoden der Organichen Chemie, Georg Thieme Verlag, Stuttgart, 1968, 10/4, 473.
46. A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223.
47. V. K. Aggarwal, E. Alonso, G. Hynd, K. M. Lydon, M. J. Palmer, M. Porcelloni, and J. R. Studley, Angew. Chem., Int. Ed. Engl., 2001, 40, 1430.
48. V. G. Nenajdenko, A. V. Shastin, V. N. Korotchenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2001, 1003 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1047].
49. V. G. Nenajdenko, A. V. Shastin, V. N. Korotchenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2001, 1003 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1047].
50. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Zh. Organ. Khim., 2003, 39, 562 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
51. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Zh. Organ. Khim., 2003, 39, 562 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
52. D. J. Burton and L. J. Kehoe, J. Org. Chem., 1970, 35, 1339.
53. D. J. Burton and L. J. Kehoe, J. Org. Chem., 1971, 36, 2596.
54. P. Martin, E. Steiner, J. Streith, T. Winkler, and D. Bellus, Tetrahedron, 1985, 41, 4057.
55. M. Assher and D. Vofsi, J. Chem. Soc. (B), 1968, 947.
56. T. Saeousa, K. Yonezawa, I. Murase, T. Konoike, S. Tomita, and I. Ito, J. Org. Chem., 1973, 38, 2319.
57. I. Ito, K. Yonezawa, and T. Saeousa, J. Org. Chem., 1974, 39, 1763.
58. B. V. Timokhin, Usp. Khim., 1990, 59, 332 [Russ. Chem. Rev., 1990, 59 (Engl. Trans.)].
59. B. V. Timokhin, Usp. Khim., 1990, 59, 332 [Russ. Chem. Rev., 1990, 59 (Engl. Trans.)].
60. K.-W. Lee and T. L. Brown, J. Am. Chem. Soc., 1987, 109, 3269.
61. N. Heinrich, W. Koch, and G. Frenking, Chem. Phys. Lett., 1986, 124, 20.
62. A. Modelli, F. Scagnolari, G. Distefano, D. Jones, and M. Guerra, J. Chem. Phys., 1992, 96, 2061.
63. R. G. Parr, L. van Szentpály, and S. Liu, J. Am. Chem. Soc., 1999, 121, 1922.
64. P. Pérez, A. Toro-Labbé, A. Aizma, and R. Contreras, J. Org. Chem., 2002, 67, 4747.
65. J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865.
66. D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.
67. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, J. Chem. Soc., Perkin Trans. 1, 2002, 883.
68. A. J. Speziale and K. W. Ratts, J. Am. Chem. Soc., 1962, 84, 854.
69. J. Villieras, P. Perriot, and J. F. Normant, Synthesis, 1975, 458.
70. S. Lebedev, Zh. Ros. Fiz.-Khim. O-va [J. Russ. Phys.-Chem. Soc.], 1900, 32, 197 (in Russian).
71. G. M. Zhdankina, G. V. Kryshtal', E. P. Serebryakov, and L. A. Yanovskaya, Izv. Akad. Nauk SSSR. Ser. Khim., 1988, 2868 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 2589 (Engl. Transl.)].
72. G. M. Zhdankina, G. V. Kryshtal', E. P. Serebryakov, and L. A. Yanovskaya, Izv. Akad. Nauk SSSR. Ser. Khim., 1988, 2868 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, 2589 (Engl. Transl.)].
73. A. Merz, Angew. Chem., 1977, 89, 54.
74. D. Seyferth and R. S. Marmor, J. Organomet. Chem., 1973, 59, 237.
75. H. O. Krabbenhoft, J. Org. Chem., 1978, 43, 1305.
76. H. Tanaka, S. Yamashita, M. Yamanoue, and S. Torii, J. Org. Chem., 1989, 54, 444.
77. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Synthesis, 2001, 2081.
78. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Organic and Biomolecular Chemistry, 2003, 1, 1906.
79. Piretroidy. Khimiko-tekhnoloicheskie aspekty [Pyrethroids. Chemical and Engineering Aspects], Ed. V. K. Promonenkov, Khimiya, Moscow, 1992, 330 pp. (in Russian).
80. E. J. Corey and P. L. Fuchs, Tetrahedron Lett., 1972, 13, 3769.
81. F. Ramirez, N. B. Desai, and N. McKelvie, J. Am. Chem. Soc., 1962, 84, 1745.
82. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2001, 1334 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1401].
83. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2001, 1334 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1401].
84. J. Uenishi, R. Kawahama, O. Yonemitsu, and J. Tsuji, J. Org. Chem., 1998, 63, 8965.
85. T. Harada, D. Hara, K. Hattori, and A. Oku, Tetrahedron Lett., 1988, 29, 3821.
86. D. R. Williams, K. Nishitani, W. Bennett, and S. Y. Sit, Tetrahedron Lett., 1981, 22, 3745.
87. T. Harada, T. Katsushira, D. Hara, Y. Kotani, K. Maejima, R. Kaji, and A. Oku, J. Org. Chem., 1993, 58, 4897.
88. J. Tsuji, Palladium Reagents and Catalysts, J. Wiley and Sons, New York, 1995.
89. J. Uenishi, R. Kawahama, Y. Izaki, and O. Yonemitsu, Tetrahedron, 2000, 56, 3493.
90. E. D. Matveeva, A. S. Erin, and A. L. Kurts, Zh. Org. Khim., 1997, 33, 1141 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].
91. E. D. Matveeva, A. S. Erin, and A. L. Kurts, Zh. Org. Khim., 1997, 33, 1141 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].
92. S. Chowdhury and S. Roy, J. Org. Chem., 1997, 62, 199.
93. C. Kuang, H. Senboki, and M. Tokuda, Synlett, 2000, 1439.
94. M. Matsumoto and K. Kuroda, Tetrahedron Lett., 1980, 21, 4021.
95. A. V. Shastin, V. N. Korotchenko, G. N. Varseev, V. G. Nenajdenko, and E. S. Balenkova, Zh. Org. Khim., 2003, 39, 433 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
96. A. V. Shastin, V. N. Korotchenko, G. N. Varseev, V. G. Nenajdenko, and E. S. Balenkova, Zh. Org. Khim., 2003, 39, 433 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
97. E. Negishi, M. Kotora, and C. Xu, J. Org. Chem., 1997, 62, 8957.
98. D. H. Barton, R. G. Bashiardes, and J. L. Fourrey, Tetrahedron, 1988, 44, 147.
99. D. E. van Horn and E. Negishi, J. Am. Chem. Soc., 1978, 100, 2252.
100. C. E. Castro and W. C. Kray, J. Am. Chem. Soc., 1966, 88, 4447.
101. R. B. Miller and T. Reichenbach, Tetrahedron Lett., 1974, 543.
102. H. P. On, W. Lewis, and G. Zweifel, Synthesis, 1981, 999.
103. J. Barluenga, L. J. Alvares-Garcia, and J. M. Gonzalez, Tetrahedron Lett., 1995, 2153.
104. N. A. Petasis and I. A. Zavialov, Tetrahedron Lett., 1996, 567.
105. Soedineniya ftora: Sintei i primenenie [Fluorine Compounds. Synthesis and Application], Ed. N. Isikawa, Mir, Moscow, 1990, 407 pp. (Russ. Transl.).
106. M. Hudlucky and A. E. Pavlath, Chemistry of Organic Fluorine Compounds II, American Chemical Society, Washington DC, 1995, 1297 pp.
107. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2001, 57, 7519.
108. M. Fujita, T. Morita, and T. Hiyama, Tetrahedron Lett., 1986, 27, 2135.
109. M. Fujita, T. Hiyama, and K. Kondo, Tetrahedron Lett., 1986, 27, 2139.
110. M. Fujita and T. Hiyama, Bull. Chem. Soc. Jpn, 1987, 60, 4377.
111. V. G. Nenajdenko, A. V. Shastin, V. N. Korotchenko, G. N. Varseev, and E. S. Balenkova, Eur. J. Org. Chem., 2003, 302.
112. C. Chen, K. Wilcoxen, N. Strack, and J. R. McCarthy, Tetrahedron Lett., 1999, 40, 827.
113. D. J. Burton and H. C. Krutzsch, J. Org. Chem., 1970, 35, 2125.
114. D. J. Burtonkova and H. C. Krutzsch, J. Org. Chem., 1971, 36, 2351.
115. M. J. van Hammekova and D. J. Burton, J. Fluorine Chem., 1977, 10, 131.
116. M. J. van Hammekova and D. J. Burton, J. Organomet. Chem., 1979, 169, 123.
117. V. G. Nenajdenko, G. N. Varseev, V. N. Korotchenko, A. V. Shastin, and E. S. Balenkova, J. Fluorine Chem., 2003, 124, 115.
118. M. J. Tozer and T. F. Herpin, Tetrahedron, 1996, 52, 8619.
119. S. I. Hayashi, T. Nakai, N. Ishikawa, D. J. Burton, and D. G. Naae, J. S. Kesling, Chem. Lett., 1979, 983.
120. D. J. Burton, J. Fluorine Chem., 1999, 100, 177.
121. B. V. Nguyen and D. J. Burton, J. Org. Chem., 1997, 62, 7758.
122. R. Ocampo, W. R. Dolbier, and R. Paredes, J. Fluorine Chem., 1998, 88, 41.
123. R. U. J. Chari and J. Wemple, Tetrahedron Lett., 1979, 111.
124. I. Nakamura and K. Harada, Heterocycles, 1978, 473.
125. I. A. McDonald, J. Lacoste, P. Bey, M. Wagner, M. Zreida, and M. G. Palfreyman, J. Am. Chem. Soc., 1984, 106, 3354.
126. A. Yu. Rulev, Usp. Khim., 1998, 67, 317 [Russ. Chem. Rev., 1998, 67 (Engl. Transl.)].
127. A. Yu. Rulev, Usp. Khim., 1998, 67, 317 [Russ. Chem. Rev., 1998, 67 (Engl. Transl.)].
128. S. Arai, K. Nakayama, Y. Suzuki, K. Hatano, and T. Shioiri, Tetrahedron Lett., 1998, 39, 9739.
129. D. J. Burton and J. R. Greenwald, Tetrahedron Lett., 1967, 1535.
130. M. Makosza, R. Podraza, and M. Bialecki, Gazz. Chim. Ital., 1995, 125, 601.
131. M. Miura, A. Hattori, and M. Nomura, J. Chem. Soc., Perkin Trans. 2, 1988, 1643.
132. J. S. Son, K. S. Jung, H. R. Kim, and J. N. Kim, Synth. Commun., 1998, 28, 1847.
133. Y. Ishino, M. Mihara, S. Nishihama, and I. Nishiguchi, Bull. Chem. Soc. Jpn, 1998, 71, 2669.
134. V. G. Nenajdenko, O. N. Lenkova, A. V. Shastin, and E. S. Balenkova, Synthesis, 2004, 573.
135. V. G. Nenajdenko, A. V. Shastin, I. V. Golubinskii, O. N. Lenkova, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2004, 218 [Russ. Chem. Bull., Int. Ed., 2004, 53, 228].
136. V. G. Nenajdenko, A. V. Shastin, I. V. Golubinskii, O. N. Lenkova, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2004, 218 [Russ. Chem. Bull., Int. Ed., 2004, 53, 228].
137. Y. Shen and S. Gao, J. Chem. Soc., Perkin Trans. 1, 1996, 2531.
138. K. Jahnisch and H. Seeboth, J. Prakt. Chem., 1981, 323, 26.
139. Y. M. Saunier, R. Danion-Bougot, D. Danion, and R. Carrie, Bull. Soc. Chim. Fr., 1976, 1963.
140. K. Schollberg, H. Schafer, and K. Gewald, J. Prakt. Chem., 1983, 325, 876.
141. H. W. Moore, F. Mercer, D. Kunert, and P. Albaugh, J. Am. Chem. Soc., 1979, 101, 5435.
142. A. J. Gordon and R. A. Ford, The Chemist's Companion. A Handbook of Practical Data, Techniques, and References, Wiley, New York - London - Sydney - Toronto, 1972.
143. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Zh. Org. Khim., 2003, 39, 562 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
144. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Zh. Org. Khim., 2003, 39, 562 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
145. V. G. Nenajdenko, V. N. Korotchenko, A. V. Shasthi, D. A. Tyurin, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2003, 1740 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1835].
146. V. G. Nenajdenko, V. N. Korotchenko, A. V. Shasthi, D. A. Tyurin, and E. S. Balenkova, Izv. Akad. Nauk. Ser. Khim., 2003, 1740 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1835].